Biomedical subjects
Publications and source records attributed to Juyoung Yoon.
A new fluorescent chemosensor based on the acridine-Zn(II) derivative effectively recognizes pyrophosphate and inorganic phosphate at pH 7.4. Acridine derivative 1 displayed a fluorescent quenching effect with pyrophosphate; on the other hand, a large fluorescent enhancement was observed with inorganic phosphate. [structure: see text].
A new fluorescein derivative 1 bearing a boronic acid group was investigated as a fluorescent chemosensor for F-. An off-on type fluorescence enhancement was observed by the blocking of the photoinduced electron transfer mechanism, which was induced by the interaction between fluoride and boronic acid moiety.
A photoinduced charge transfer (PCT)-based 1,3-alternate calix[4]crown fluoroionophore containing two cation recognition sites, a crown ether ring and two facing pyreneamide groups, is synthesized. Upon addition of K+, Pb2+, or Cu2+, wavelength changes are observed in both the fluorescence and absorption spectra, but with different binding modes. With K+, fluorescence emissions of the ligand scarcely change, while addition of Pb2+ or Cu2+ produces a remarkable change in both the excimer and monomer emissions. The observed data indicate that the metal cation is encapsulated in the crown-5 ring for K+ and by the two facing amide groups in the latter case, which is verified by a metal ion exchange experiment. The wavelength shifts in both fluorescence and absorption spectra upon addition of Cu2+ show that, in contrast to Pb2+, Cu2+ interacts with the nitrogen atoms of the amide groups, resulting in a PCT mechanism.
New 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) derivatives (1 and 2) were synthesized as an "off-on" fluorescent chemosensor and fluorescent chemodosimeter for Cu2+ and Pb2+. Compound 1 displayed selective and large chelation enhanced fluorescence effects with Pb2+ and Cu2+ among the metal ions examined. On the other hand, compound 2, a fluorescent chemodosimeter, effectively recognized Cu2+ via a selective hydrolysis of the acetyl group.
This tutorial review covers imidazolium receptors for anion recognition according to their topological and structural classification, and includes benzene tripodal, cyclophane and calix-imidazolium, fluorescent imidazolium, ferrocenyl imidazolium, cavitand and calixarene, and polymeric imidazolium systems.
[Structure: see text]. This study demonstrated that Zinpyr-1*Zn2+ acts as a fluorescent and colorimetric sensor for pyrophosphate at pH 7.4. In addition, Zinpyr-1*Cu2+ and DIARB-1*Cu2+ complexes were found to act as selective fluorescent sensors for pyrophosphate. Furthermore, the chemosensors Zinpyr-1*Zn2+ and Zinpyr-1*Cu2+ show highly selective and ratiometric fluorescence changes for pyrophosphate compared with H2PO4-.
A new fluorescent sensor based on rhodamine B for Pb2+ was synthesized. The new fluorescent sensor showed an extreme selectivity for Pb2+ over other metal ions examined in acetonitrile. Upon the addition of Pb2+, an overall emission change of 100-fold was observed, and the selectivity was calculated to be 200 times that of Zn2+. The signal transduction occurs via of reversible CHEF (chelation-enhanced fluorescence) with this inherent quenching metal ion.
[structure: see text] A new cavitand bearing four imidazolium groups was synthesized for the recognition of anions through (C-H)+...X- hydrogen bond formation. The binding properties toward various anions including dicarboxylates were examined on the basis of 1H NMR spectroscopic experiments.
A new water-soluble imidazolium anthracene derivative not only differentiates two structurally similar compounds GTP and ATP but also acts as potential fluorescent chemosensors (as a quencher and an enhancer, respectively) for GTP and ATP in 100% aqueous solution (pH = 7.4, 10 mM HEPES).
Unique hydrogen bonds of the 9-H of anthracene moieties in hosts 1 and 2 with fluoride and pyrophosphate ions were observed on the basis of the (1)H NMR experiments. Furthermore, hosts 1 and 2 act as a colorimetric sensor and a fluorescent chemosensor for the recognition of fluoride ion, respectively.
A new anthracene dimer connected by two imidazolium moieties has been systematically designed and synthesized as a fluorescent chemosensor for selective binding of H(2)PO(4)(-) over other anions, which have been examined using fluorescence and (1)H NMR and rationalized with ab initio study.
Unexpected syn beta-amino-alpha-bromination of unsaturated phosphonates was observed under typical Sharpless AA reaction conditions with excess N-bromoacetamide.
A new naphthalene derivative containing a urea group at the 1,8-position of naphthalene was synthesized and showed a unique absorption and fluorescence peak with a fluoride ion. Calculations suggested that a new peak was attributed to the increased anion character of urea nitrogen due to the strong interaction of the fluoride and N-H protons.
[structure: see text] The fluorescent chemosensor 1 bearing two imidazolium groups at the 1,8-position of anthracene has been designed for the recognition of anions through the (C-H)(+)- - -X(-) hydrogen bond formation. As unique tweezer-like binding of 1 with anions is predicted by the ab initio calculations, strong anion-binding properties of chemosensor 1 are demonstrated by using fluorescence as well as (1)H NMR.
A benzene-based tripodal imidazolium receptor utilizing the strong (C-H)(+)...X(-) hydrogen bonding interaction between imidazolium moieties and halide anions is extensively investigated both theoretically and experimentally. Ab initio calculations predict that this receptor has a very high affinity for fluoride ion (F(-)). The association constant and free energy gain of the N-butyl receptor 2 for F(-) in acetonitrile were measured to be 2.1 x 10(5) M(-1) and -7.25 kcal/mol, respectively, showing that the receptor has a high affinity for F(-) in highly polar organic solvents.
[structure: see text] In consideration of competition between cation-pi and hydrogen bond interaction forces, we designed a novel receptor, 1,3,5-tris(pyrrolyl)benzene, which shows high selectivity for acetylcholine (ACh). The selectivity of the receptor for ACh over other ammonium cations is demonstrated by the ion-selective electrode (ISE) method in buffer solution. The binding free energy of the receptor with ACh in chloroform solution is measured to be 3.65 kcal/mol in the presence of chloride anion by nuclear magnetic resonance spectroscopy, and that in water is estimated to be much greater ( approximately 6 kcal/mol).
Synthesis and binding studies of a new calixarene-based fluoroionophore were made. Calix[4]azacrown having an anthracenyl unit displayed large chelation-enhanced fluorescence effects with Cs(+), Rb(+), and K(+) over other metal ion tested. Interesting "molecular taekwondo" processes between Cs(+)-Cu(2+) and Cs(+)-Ag(+) pairs were monitored via fluorescent changes.
New fluorescent chemosensors, 1,8-bis(pyrazolylmethyl)anthracene and 9,10-bis(pyrazolylmethyl)anthracene, were synthesized. The 1,8-isomer showed selective fluorescent quenching effects with Ag(I) and Cu(II). On the other hand, the 9,10-isomer displayed a selective fluorescent quenching effect only with Ag(I). From the association constants obtained from fluorescent titrations and by extraction, we conclude that rigid immobilization of the ligands, 1,8-isomer, plays a more important role in the binding with Ag(I) than the additional pi-cation interaction offered by the 9,10-isomer.